Amphiphilic drug interactions with model cellular membranes are influenced by lipid chain-melting temperature

J R Soc Interface. 2014 Mar 12;11(94):20131062. doi: 10.1098/rsif.2013.1062. Print 2014 May 6.

Abstract

Small-molecule amphiphilic species such as many drug molecules frequently exhibit low-to-negligible aqueous solubility, and generally have no identified transport proteins assisting their distribution, yet are able to rapidly penetrate significant distances into patient tissue and even cross the blood-brain barrier. Previous work has identified a mechanism of translocation driven by acid-catalysed lipid hydrolysis of biological membranes, a process which is catalysed by the presence of cationic amphiphilic drug molecules. In this study, the interactions of raclopride, a model amphiphilic drug, were investigated with mixtures of biologically relevant lipids across a range of compositions, revealing the influence of the chain-melting temperature of the lipids upon the rate of acyl hydrolysis.

Keywords: drug transport; high-performance liquid chromatography; lipid hydrolysis; membrane biophysics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Transport
  • Blood-Brain Barrier / chemistry
  • Hydrolysis
  • Membrane Lipids / chemistry*
  • Membranes, Artificial*
  • Models, Chemical*
  • Raclopride / chemistry*

Substances

  • Membrane Lipids
  • Membranes, Artificial
  • Raclopride